Former ‘Girlfriend No.1’ reveals life at Playboy Mansion

The party is finally over. The King is dead. The lights are off in the Playboy Mansion and all that’s left are the stories – of how Hugh Hefner, the Godfather of Sex, and his vision of bountiful free love, had conquered a nation. And created a life of barely believable glamour in the process.

Except that it wasn’t. The sexy fairytale Hef would have you believe in was a bedazzled, twisted, toxic prison. And I know that because I spent six years as Girlfriend Number One to a man old enough to be my grandfather.

How could I justify such a thing? ‘I’m here for adventure, a once-in-a-lifetime experience. I’m here as a stepping-stone to something else,’ I told myself. And then perhaps the biggest illusion of all: ‘I’m here for love.’

Holly Madison became Hugh Hefner’s no.1 girlfriend in 2001, when she was just 21

Deeper and deeper I fell down the rabbit hole.

My story wasn’t atypical: a small-town girl who dreamt of becoming someone special. I moved to Los Angeles to go to college and got a job waitressing at the Hooters Bar – featuring busty waitresses – a job that resulted in an invitation to a party at the Playboy Mansion.

For a starstruck girl from Oregon, this felt like the chance of a lifetime. The dress code was strict: ‘Sleepwear Required.’ Despite having very little income, I bought a lingerie set from Frederick’s of Hollywood: a black satin corset with matching garter belts, thigh-high stockings, and a short silk robe.

When I arrived with my friend Heather, every inch of the estate seemed to sparkle. ‘Oh my god, there’s Cameron Diaz,’ Heather said, pointing to a tall beautiful blonde. Next to her was Jim Carrey. Across the pool, Heather spotted Leonardo DiCaprio!

We walked through the infamous candlelit grotto – still empty at this early hour – and the zoo. Everything looked so sensuous and inviting.

Tucked away in a corner of a tent our host looked gloomy for a man flanked by two of the most breathtaking beauties I had ever seen. My first thought was that he was out of it. Was he senile? Or just bored?

Maybe Mr Playboy would suggest I audition for his magazine? ‘Hi, I’m Holly,’ I said. ‘What’s that?’ he asked.

‘I’m Holly,’ I repeated, a little louder. ‘Oh, hi. Nice to meet you, darling,’ Hef said before turning his attention to the next person.

Oh well, I thought, I gave it a shot. Somehow my presence had been overlooked. But there were more invitations, more parties, and a year later, I had become something of a fixture at the mansion.

What wasn’t to love? Bikinis, drinks, food, music, and friends. It was a life so unlike my own that I almost envied the women who called this magical place home.

No.1 Girlfriend: Madison was flattered to be one of 20 or so girls invited to the smaller Sunday pool parties

I was flattered to be one of 20 or so girls invited to the smaller Sunday pool parties. When the light dipped below the hills, the festivities moved inside.

Eventually, his harem of girlfriends would trickle down to take their seats next to Hef at the dining table. I could never understand their lack of enthusiasm. Initially, I assumed they were spoiled, jaded, or just not a good fit in Hef’s world.

This may sound naïve, but I didn’t immediately realise that they were actually required to sleep with him.

My main focus was pursuing an acting career, but it’s almost unsettling how quickly your priorities can shift.

The desire to perform is what had first driven me to Los Angeles and, as the lease on my apartment neared its end, the thought of returning home almost killed me.

I started to wonder, couldn’t Playboy help me reach that goal? The more time I spent there, the whole girlfriend thing began to look appealing. Around that time, I was invited to join Hef on one of his biweekly club nights.

I was one of the first to step out of the limo and every set of eyes turned to check if I was someone worth knowing. When Hef finally emerged from the car, the crowd went wild. He lifted a hand as if he were some kind of dignitary.

We were whisked away to a private area next to the dance floor. To an outsider, it must have looked incredibly glamorous: seven beautiful women dancing away behind velvet ropes with private table service to cater to our every desire – all at Hef’s expense.

But if you looked close enough, each girl appeared to be just a little bit vacant.

When Hef stood up to dance, his rhythm was so off that I let out a big laugh. I wondered why these women didn’t care enough to protect him from the embarrassment—surely they owed him that? Back at the table, he leaned towards me with a bunch of large horse pills in his hands.

‘Would you like a Quaalude? Hef asked. ‘No thanks,’ I answered cheerfully. ‘I don’t do drugs.’

‘That’s good, he said nonchalantly. ‘Usually I don’t approve, but in the Seventies they used to call these pills “thigh openers”.’

Today, I want to scream ‘PAUSE!’ and freeze frame that moment in late August 2001. I want to grab that young girl, shake her and demand: ‘What the hell are you thinking?’ Why didn’t I run for the nearest exit? I suppose I had already made up my mind at that point. If I became a girlfriend, I would have somewhere to live. If I became part of Playboy’s inner circle, perhaps that could help my career.

On the limo ride back to the mansion, Candice leaned over and whispered to me that all of the girls were expected to join Hef in his bedroom. Foolishly, I was extremely drunk and what happened next is best not dwelt upon. Suffice it to say that the next morning, I felt terrible and it wasn’t just the hangover. I was freaked out and ashamed.

It might be hard to understand but in that moment, I didn’t blame Hef for the creepy night before. He had the ‘nice guy’ act down pat. Besides, I was young, vulnerable and foolish – and I needed somewhere to stay.

‘Can I ask you something?’ He looked up and I told him that I had no place to live. ‘What do you think about me moving in?’

He paused and replied: ‘You can stay for a while and we’ll see how it works out.’

No one gave me a tour of the mansion, so I kept discovering new places for myself. The secret passage from the main house to the gym, the panel in the living-room wall that revealed a secret wine cellar used as a speakeasy in the 1920s. There was an attic office with adjacent bathroom that looked like a time capsule, with gold shag carpet and an untouched tray of toiletries from the 1970s. The taps were naked ladies.

The mansion may have looked like 1970s porn chic, but it was neglected. There were nine dogs and the ancient yellow carpet on the grand staircase was covered in their urine stains.

In less than a year Hefner (pictured with Playboy in 2007) had promoted Madison to his ‘main’ girlfriend

There was a strict routine. Monday was ‘Manly Night’, when Hef would have his male friends over for a movie. Tuesday was ‘Family Night’ for his wife and two sons. Wednesday and Friday were ‘Club Nights.’ On Thursday (like Monday and Tuesday) we could do as we pleased. Saturday was a buffet dinner and movie with Hef. Sunday was a pool party during the day, and dinner and a movie at night.

There were many rules. First, there was a curfew – Hef required his girlfriends to be in by 9pm. We were not allowed to fraternise with the staff. Each girlfriend was given a weekly clothing allowance of $1,000. The last major requirement was that girlfriends attend all Hef’s events.

I was too naïve to realise it at the time, but Hef wanted to have us wallowing in our own insecurities and pawing for his acceptance. Girlfriends that didn’t get along gave him the feeling of being fought over and desired, something he was desperate to feel in his old age.

I’d always been confident, but it didn’t take long for my self-worth to start to crumble. He was cruelly manipulative, happy to reduce me to tears. ‘Don’t ever wear red lipstick again,’ he once warned me in a low voice. ‘You look old, hard, and cheap.’

I was so constantly on edge that I eventually developed a stammer so I tried as best I could to stay quiet.

To Hef, this was a sign of submission that helped me become one of his favourites. And I developed my own brand of Stockholm syndrome, identifying with my captor. It didn’t seem to matter that I couldn’t recall how or why.

In less than a year, Hef had promoted me to his ‘main’ girlfriend. There was nothing ceremonial: Hef simply asked if I wanted to move in-to his room. That was it. No promises were made; no token jewellery given. The only difference was that he often said ‘I love you’, and started referring to me as the ‘love of his life’.

Meanwhile the girls were becoming increasingly hostile. I noticed a piece of paper taped over a vent on Vicky’s bedroom wall. ‘What’s that?’ I asked. ‘The girls who were in here last night put that up,’ she explained. ‘They were up here smoking meth and it has a really foul smell.’

Speaking of the other girls, Vicky added: ‘You know I can’t stand Dianna, right? You know how when you do coke, there’s a pile in the centre with some lines next to it for people to do?’ I nodded. I didn’t do it myself, but cocaine was the drug of choice for the girl.

‘Well, Dianna does the whole f*****g pile! And you know Amanda?’ she asked, jumping to the next subject. ‘Well, she makes a lot of money. Thousands of dollars a night. Actually, almost all of the Playmates make that kind of money.’

‘No way!’ I shouted. Rumours of Playmates working for escort agencies had circulated for decades, but I’d never heard it first hand before.

‘Yeah,’ Vicky said with a carefree laugh. ‘Everybody does it… do you think it might be something you’d be interested in?’ ‘No way!’ I said.

Was she really asking me to become a hooker!?

After seven years living under Hef’s strict rules, I had tried to rationalise the choices I had made by convincing myself that I had fallen in love, and wanted to settle down and have a family, which was perhaps my subconscious attempt to end the relationship.

Hef had submitted semen samples to a fertility doctor, only to find that nothing from this 70-something-year-old man was viable – proof that there really was no future for me at the mansion.

By now, his harem was dwindling. Once I had dreamed of being ‘the only one’, now I was starting to panic. Also, I was finally seeing Hef’s true colours.

After one trivial disagreement, he began shouting at me and his hands clenched into fists. My mouth fell open in shock. After what felt like 30 seconds, he stomped his foot and scuffled away.

A few days later, I flew to Las Vegas for a two-day photoshoot – and a rare night alone. When I awoke the next morning, the last thing I expected was to have a ferociously angry Hef on the phone shouting: ‘Thank you for giving me the WORST night of my life! You had a guy in your room last night!’

I paused. He had actually had me followed. ‘Nothing happened,’ I said firmly. ‘I had a few drinks and a friend walked me in to make sure I got into bed OK. That’s it.’ And it really was.

Returning to LA, I was determined to make my exit as quickly as possible. The mansion wasn’t a magical place any more.

I had peeked behind the curtain and saw the frail old man pretending to be someone he wasn’t.